The catalytic influence of clays on Bamberger rearrangement: Unexpected formation of p-nitrosodiphenyl amine from N-phenylhydroxylamine

Catalysis Letters

Volumn 54, Issue 3, 1998, Pages 165-167

  Naicker, Kannan P ^a,b   Pitchumani, Kasi ^a   Varma, Rajender S ^b  

^a MADURAI KAMARAJ UNIVERSITY   (India)

^b SAM HOUSTON STATE UNIVERSITY   (United States)

Author keywords

Bamberger rearrangement; Catalysis; Cation exchanged clays; Montmorillonite K 10 clay; P nitrosodiphenyl amine; Unexpected product

Indexed keywords

EID: 0041696235     PISSN: 1011372X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1019060829242     Document Type: Article

References (25)

1. E. Bamberger, Ber. 27 (1894) 1347.
2. E. Bamberger, Ber. 27 (1894) 1548.
3. E. Bamberger and J. Lagutt, Ber. 31 (1898) 1500.
4. E. Bamberger, Ber 28 (1895) 245.
5. E. Bamberger, Ber 33 (1900) 3600.
6. (a) T.J. Pinnavia, Science 220 (1983) 4595;
7. (b) P. Laszlo, Science 235 (1987) 1473.
8. (a) J.M. Adams, S.E. Davies, S.H. Graham and J.M. Thomas, J. Catal. 78 (1982) 197;
9. (b) J.A. Ballantine, J.H. Purnell and J.M. Thomas, Clay Mineral 18 (1983) 347.
10. (a) J.A. Ballantine, M. Davies, H. Purnell, M. Rayanakorn, J.M. Thomas and K.J. Williams, J. Chem. Soc. Chem. Commun. (1981) 8;
11. (b) R. Burch and C.I. Warburton, J. Catal. 97 (1986) 511;
12. (c) O. Sieskind and P. Albrecht. Tetrahedron Lett. 26 (1985) 2135.
13. J. Tateiwa, H. Horiuchi, K. Hashimoto, T. Yamauchi and S. Uemura, J. Org. Chem. 59 (1994) 5901.
14. (a) C.G. Bruce, in: Materials Chemistry (1995) p. 301;
15. (b) J. Cabral, P. Laszlo and M.T. Montaufier, Tetrahedron Lett. 29 (1988) 547.
16. (a) P. Kannan, K. Pitchumani, S. Rajagopal and C. Srinivasan, J. Chem. Soc. Chem. Commun. (1996) 369;
17. (b) P. Kannan and K. Pitchumani, Catal. Lett. 45 (1997) 271;
18. (c) P. Kannan, K. Pitchumani, S. Rajagopal and C. Srinivasan, J. Mol. Catal. 118 (1997) 189;
19. (d) R.S. Varma and K.P. Naicker, Tetrahedron Lett. 39 (1998) 2915;
20. (e) R.S. Varma, K.P. Naicker and J.P. Liesen, Tetrahedron Lett. 39 (1998) 3977.
21. A. Cornells and P. Laszlo, Synthesis (1985) 909.
22. O. Kamm, Organic Synthesis, Coll. Vol. I, 2nd Ed. (Wiley, New York, 1956) p. 445.
23. D.R. Levering and L.G. Maury, US Patent 3,090,786 (1963); CA 59, 12770b (1963)
24. K. Hirayama, Handbook of Ultraviolet and Visible Absorption Spectra of Organic Compounds (Plenum Press Data, New York, 1967) p. 200.
25. A.I. Vogel, Textbook of Practical Organic Chemistry, 3rd Ed. (Longman, London, 1956) p. 1085.